Even for the most skilled dressers, assembling a killer outfit sometimes requires a little more inspiration than the average online shopping experience provides. Enter Roxana Altamirano, the genius behind Nerd Boyfriend, the style blog that offers step-by-step instructions for recreating ensembles worn by icons ranging from Ingmar Bergman to Willie Nelson. Now she's guest blogging on Details.com every week. Have a hero you want to see featured? Just leave a note in the comments, and we'll see what we can do.
Never prone to bold statement with their style choices, Simon & Garfunkel outfit themselves with clean-cut, classic looks. So follow their lead by heading over to your father or grandfather's closet to pick out your new favorites: windbreaker, black turtleneck, wool trousers, short chinos, and worn-in boots.
On bottom, try a pair of gray wool trousers like these from Billy Reid.
Black leather derby shoes from ASOS.
If Paul Simon (right) is more your style, you can find a wool topcoat like his at Jos. A. Bank.
Top off the outfit with a pair of vintage-inspired, lace-up boots like these from Urban Outfitters.